I Should've Known
by avan337
Summary: After Rich turns her down, Annie spends a night drinking wine and listening to Taylor Swift's "Speak Now" CD
1. Chapter 1

_This started out with me changing up the words to "Dear John," then I got to thinking that Annie would probably listen to Taylor Swift. Then it became a challenge to use all of the songs on the CD. I hope you find the funny mixed in with the maudlin._

**I Should've Known**

Annie sat in her car in the Greendale parking lot, crying as she sent the text to Abed. Once again, she had put herself out there for a guy, and once again she was humiliated.

At least Rich had let her down more gently than Jeff. She couldn't even get mad at Rich: he _was_ the perfect guy. Suddenly she found that to be more annoying than charming.

Annie wished she had some wine at home. Grownups got drunk after getting their hearts broken, right? But she couldn't buy her own liquor, and she wasn't about to ask for help from anyone in the group.

Her eyes lit up as she remembered that Annie Edison couldn't buy alcohol, but Caroline Decker from Corpus Christi, 78418, sure as hell could. Wiping off her tears, she started her car and roared away from Greendale.

* * *

Back in her apartment, after downing a glass of merlot, Annie decided this pity party needed some music. When she turned on her iPod, she saw it was set to "Love Story" by Taylor Swift, and she remembered how hopeful she was on the way to class this morning, thinking she had finally landed on the right guy.

Snorting in disgust, she flipped up to _Speak Now_ and heard the intro to _Mine_. "Oh, great, two people who meet in college having a happy ending," she grumbled as she hit the forward button, "just what I need."

* * *

Flip – _Sparks Fly_

Annie poured herself another glass of wine as the lyrics began.

_You're the kind of reckless that should send me running  
__But I kinda know that I won't get far_

_And you stood there in front of me just  
__Close enough to touch _

She had been so close to Jeff earlier. Sure, it was pretty crazy walking into the men's bathroom, but she had to know what was going on with him. Or rather, she already knew; she just wanted him to say it. But he refused to admit he was jealous, and he refused to admit he had feelings for her.

But he never said he _didn't_ have feelings for her, either…

"Stupid Jeff Winger and his stupid…talking…skills," she muttered angrily.

* * *

Flip – _Back to December_

Oh, December, when she had helped dredge the river with Rich. Rich had brought a candle to place in her Egg McMuffin for her birthday. It was the morning they picked up trash in the park. He was so sweet, so thoughtful, so good.

More muttering: "Stupid Rich and his stupid goodness. And his stupid kettle corn."

* * *

Flip – _Speak Now_

_I'm am not the kind of girl, who should be rudely barging in on a white veiled occasion_

Trouble was, Annie knew she _was_ that kind of girl. If Jeff were marrying someone, she would probably barge in on the wedding to stop it. Well, she would be invited, so she wouldn't have to barge in.

"He would invite me, right?"

Nope, that wasn't the point, she reminded herself. The point was, Jeff shouldn't be getting married. He shouldn't be getting married to anyone else…

Shaking her head, she took a big gulp of wine and put the image of Jeff in a tux, waiting at the end of a church aisle, out of her head.

* * *

Flip – _Dear John_

"Oh, here we go!" Annie shouted in triumph, turning up the volume. "John Mayer did you wrong, Taylor, and Jeff Winger has done me wrong, too! Sucky, commitment-phobic, thirty-something year old men! Here's to the young girls fighting back!"

She opened her eyes slowly, embarrassed to find she had thrust her fist in the air and yelled to absolutely no one.

_I lived in your chess game, but you changed the rules every day_

Annie uncrossed her legs and made herself comfortable as she sang along, changing the words as she got to the first chorus.

"Dear Jeff, I see it all now it was wrong  
Don't you think I was too young to be messed with  
The girl in the dress is smarter than you

"Dear Jeff, you lied to me in the bathroom,  
Don't you think I know you better than that, douche bag"

She was really getting into it now, raising her glass in the air and swaying it back and forth.

"Well maybe it's me and my blind optimism to blame  
Or maybe it's you and your sick need to kiss me then pretend it didn't happen

"And you try to act like you don't care that I want someone else  
But you'll look back with regret  
When I finally find a man who loves meeee

"Don't you think 19's too young to be played by your dark, twisted games  
When I loved you so,  
I should've known, Jefffff…"

"Wa-hoo!" she yelped in her best Texas accent as the song ended.

* * *

Flip - _Mean_

Rich wasn't mean. Why wasn't he mean? Didn't he ever get angry? Didn't he ever want to scream at the top of his lungs because his pen kept getting stolen?

She heard Jeff's voice: "No one can be this good of a person."

Jeff certainly wasn't that good of a person, and he had been mean to her on more than one occasion.

_You, with your words like knives  
__And swords and weapons that you use against me,  
__You, have knocked me off my feet again,  
__Got me feeling like I'm nothing_

Why was she so willing to overlook that?

"Because he's…Jeff Winger," she whispered.

_And I can see you years from now in a bar,  
__Talking over a football game,  
__With that same big loud opinion but,  
__Nobody's listening,  
__Washed up and ranting about the same old bitter things_

Annie snorted out a laugh at the thought of an old, fat, drunk Jeff Winger sitting alone in a bar. That would be a fitting ending for the Jeff who left her hanging after the Transfer Dance, and again tonight in the bathroom.

But her friend Jeff deserved better, she thought sadly.


	2. Chapter 2

Flip - _The Story of Us_

_I used to know my place was a spot next to you  
__Now I'm searching the room for an empty seat  
__Cause lately I don't even know what page you're on_

Annie thought strategically of where she would sit in Anthropology on Monday. Shirley would let her sit next to her if Annie asked, and Abed would be okay with trading. He would like sitting next to Jeff. And Rich.

Rich and Jeff.

Drink.

Jeff and Rich.

Drink.

Annie had just created her own Drinking Game for One.

_So many things that I wish you knew  
__So many walls up, I can't break through_

She never would have embarrassed herself by asking out Rich if Jeff had told her how he felt. Of course, if Jeff had said he wanted her, she would have forgotten about Rich in a heartbeat.

Yeah, she was ready to move on from this song.

* * *

Flip – _Never Grow Up_

"Pssshhhh," Annie sputtered. "Never grow up, my ass."

She had been trying to grow up since she was five. Now that she was (almost) technically a grown up, she wondered if it was all it was cracked up to be.

"At least grownups can get alcohol," she smiled ruefully, twirling around the wine in her glass.

* * *

Flip – _Enchanted_

_All I can say is I was enchanted to meet you_

Rich, Rich was enchanting. Jeff was…infuriating. So this song should make her think about Rich.

_This night is sparkling, don't you let it go  
__I'm wonderstruck, blushing all the way home_

Only her mind kept drifting back to that night in May and the feel of Jeff's lips on hers and his arms around her. "Damn it!" she spat out, shocking herself.

_Please don't be in love with someone else  
__Please don't have somebody waiting on you_

Last year, it hadn't taken long for Jeff to move from Britta to Professor Slater. Annie wondered how long it would be before he forgot all about his jealously over Rich and started dating someone else.

The thought made her as nauseous as the day she had to watch him and Britta making out after they professed their fake love for each other.

"Definitely time for more wine," she said as she reached for the bottle.

* * *

Flip – _Better Than Revenge_

_There is nothing I do better than revenge_

"Ah, I feel ya, Taylor!" Annie pounded her fist against her heart in female solidarity.

How could she get revenge on Jeff? She thought that dating someone else might be the best revenge, but that idea got blown to hell. No, revenge could damage their relationship – "friendship" she corrected herself out loud – forever, and permanently alter the group.

Nope. She might do revenge really well, but it wouldn't work here. Hmm.

* * *

Flip – _Innocent_

"Oh, this is that Kanye West song."

If Taylor Swift could forgive Kanye for humiliating her in front of the world, couldn't she forgive Jeff for being himself?

_It's okay, life is a tough crowd  
__32 and still growing up now_

Jeff was looking at 32 in his rearview mirror, but he still did have a lot of growing up to do. It was ironic, the way he harped on their age difference, when they both knew she was more mature than him in a lot of ways.

_Who you are is not what you did  
__You're still an innocent_

Annie had always believed that Jeff was really a good person, deep down. And there had been times when she'd seen that side of him. So how could she write him off completely just because he didn't want to be with her, or didn't want to admit that he wanted to be with her.

Oh, who was she kidding? Annie Edison wasn't going to write off Jeff Winger anytime soon.


	3. Chapter 3

Flip – _Haunted_

_C'mon, c'mon don't leave me like this  
__I thought I had you figured out_

_Something's gone terribly wrong  
__You're all I wanted_

She tried to remember how she went from being in love with Troy, to being in love with Jeff, to being smitten with Rich. Maybe she had never really loved Troy. Maybe she had never really loved Jeff.

Annie started to wonder if she was as bad as Jeff and Britta, just wanting what she couldn't have. Yet, of all three guys, the only one who had seemed to like her back was Jeff.

Huh. Even if he didn't want a romantic relationship with her (and he never _said_ that, remember?), Jeff Winger really liked her. How 'bout them apples?

"Suck it, Riverside High!" she said, raising her glass in salute.

* * *

Flip – _Last Kiss_

_Never thought we'd have a last kiss_

Annie never imagined she would have a first kiss with Jeff. It did, indeed, seem ridiculous. Until that look he gave her when she let her hair down. After that, she was slightly curious.

During the debate, she was really thinking only of winning. It was a desperate move, a gamble that worked. She hadn't expected Jeff to fully react, to kiss her back. Maybe he had been curious, too.

Or maybe Abed really was an evil wizard.

_All that I know is I don't know how to be something you miss_

The kiss after the Transfer Dance was just as impulsive. She was lost in the moment. And once again, she was surprised when Jeff kissed her back. But he did.

Damn him, he kept kissing her back.

_Never thought we'd have a last kiss  
__Never imagine we'd end like this_

Maybe if she had kissed him in the bathroom, he would have kissed her back. Maybe not. Annie would never know.

But she did know it was time that _she_ stopped kissing _him_. If Jeff Winger wanted to kiss her again, he would have to be the kisser, not the kissee.

So yeah, that Transfer Dance kiss was probably their last.

* * *

Flip – _Long Live_

Just as the song started, Annie's cell rang. It was Britta.

"Hey, Britta!" she smiled into her phone.

"Hey, Annie, I was just calling to see if you are okay."

"I'm fine, thanks," she slurred in response.

Britta's voice was laced with concern. "Have you been drinking?"

"Me? Drink? Alone?" Annie laughed a little hysterically then belched loudly. "Well, maybe a little."

"Do you need me to come over there?"

Annie wanted to scream yes, but she held back, having had enough rejection tonight. "No, it's okay," she answered meekly.

Britta, however, saw right through her. "I'm coming over. What are you doing, anyway?"

"Oh, just listening to a little music," Annie answered.

"Have you eaten?"

"Nope. What goes with red wine?" she asked, giggling.

"Oh, good grief," Britta muttered under her breath. "Just hang on, Annie, I'll pick something up for you. And NO MORE DRINKING!"

Annie cut off her phone and sat there quietly for a few moments.

_Long live all the magic we made  
__And bring on all the pretenders  
__One day, the world will remember_

_Long live all the mountains we moved  
__I had the time of my life fighting dragons with you_

Yes, long live their little study group; their little family. Annie knew she would get over Jeff, just like she got over Troy. And things would go on as normal.

And that was okay, at least for tonight. She had a friend, someone who genuinely cared about her, who was on her way.

"Girl power, Taylor!" Annie cried as she turned off the iPod.

* * *

She had managed to pick herself up off the floor and bring the almost empty bottle of wine to the kitchen by the time Britta showed up, fast food bag in hand.

"Here," her friend said, shoving the bag into her hands. "Eat this, and I'll make coffee."

"Thanks, Britta," Annie said, giving her a hug before diving into the fries. "Hey, wanna hear a song I made up about Jeff?"

"A song you made up about Jeff while drinking an entire bottle of wine? Yes, definitely," Britta said, smiling as she closed the door behind her.


End file.
